Addendum Additional New Aporphines

The following aporphine alkaloids have been isolated and characterized after the main part of this review was written. 

The noraporphine nandigerine, C18H17O4N, was isolated from Hernandia ovigera L. (Hernandiaceae). The base crystallized from methanol either as solvent free needles (mp 176°-177° [ajp - -248° in ethanol), or as plates of the methanol solvate, C]8Hi704N-CH30H (mp 99°-100°). The alkaloid hydrochloride salt melted at 245°-247° (decomp.) (33b). 

is consistent with its formulation as an 11-substituted aporphine. The NMR-spectrum in deuteriochloroform revealed the presence of three aromatic protons (3.16-3.39 t), one methylenedioxy group (close doublet at 3.99 and 4.18 t), one methoxyl (6.40 t), and the absence of an i 7-methyl function. 

Ovigerine, obtained from Hernandia ovigera, crystallized only as the hydrochloride, CigHi504N-HCl (mp 300° decomp. [aj -P 177° in H2O). The UV-spectrum of this salt, 317, 270, 234 mp. (log e 3.77, 4.10, and 4.29), was suggestive of a 1,11-substituted aporphine. The NMR-spectrum of the free base showed no signals characteristic of either X-methyl or methoxyl, but complex signals characteristic of two superimposed methylenedioxy groups appeared centered at 4.12 and 3.99 t. 

The two methoxyls in hernovine are assumed to be at positions 1 and 11 of the aporphine system, since they appear in the NMR-spectrum of N-methylhernovine at relatively high fields (6.57 and 6.50 t) 33b). 

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